Transfrom Tool Bounding Box

The transform tool draws a bounding box around an object relative to the stage (global). Is there a way display the a bounding box relative to the object (local)?

For example, I drew a rectangle and set the pivot point to one side. (fig. 01)

Using the transform tool, I rotated at a 45° angle. (fig. 02)

As long as I do not de-select the drawing, I can continue applying transforms to the original bounding box.

If I do anything to de-select the drawing, the next time I select it with the transform tool, a new bounding box is drawn around it which is “square” to the stage (global space). (fig. 03)

Any scaling done to the drawing at this point will introduce distortion. e.g. I cannot scale in local X and Y to squash and stretch the rectangle. All transforms are global, so scaling in X and Y will also skew the rectangle, which will require counter-animating the skew value to correct for distortion.

I tried parenting the rectangle to a Peg and applying the rotation to the peg only, thinking that maybe it would preserve the scale bounding box local to the rectangle, but it did not.

Is there a feature or method that I am overlooking?